Vacation rentals with a pool in Charlottesville

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Charlottesville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Cottage in Charlottesville

4.86 out of 5 average rating, 79 reviews

Ridgeview Cottage: Mtn Views and Summer Pool!

This luxury cottage is perfectly situated between Charlottesville and VA wine country on a scenic by-way, offering 4 acres of impressive fall foliage and sweeping mountain views, grill, fire pit, and summer pool access. Located 5 miles from Foxfield and 20 minutes to UVA. Ideal for couples, but can easily accommodate two couples or a small family-- this location offers the best of both; a rural setting with outdoor amenities, yet a short drive to restaurants, shops, breweries, grounds and more.

Superhost

Home in Wintergreen Resort

4.79 out of 5 average rating, 101 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. 5min drive to slopes. ★3,500sqft on 3 floors ★Hot tub for 8 people ★Sound system ★2-Story vaulted ceiling, gas fireplace, 55” TV ★Movie room: 65” TV, pool table, wet bar, wine fridge ★Dining table seats 10 ★Desk and FAST WiFi ★Roku TV in every bedroom ★Park 6 cars Seasonal outdoor pool/tennis. Resort access not included.

Top guest favorite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 119 reviews

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.

Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Superhost

Apartment in McGaheysville

4.84 out of 5 average rating, 252 reviews

Massanutten Cozy Condo with Hot Tub & Jacuzzi

Luxury Apartment ideal for families with little kids in Massanutten. There is a huge deck with private 5-person Hot Tub and small playground on it. It is located only 5 minutes away from the ski lodge, go karts, bumping cars, Mini Golf.The Campfire Grill Restaurant is only 2 minutes away. The indoor and outdoor Water park is 8 minutes away. A gorgeous and spacious retreat in the best location for skiing/snowboarding, exploring the resort, hiking, relaxing, and enjoying the fresh mountain air.

Top guest favorite

Home in Wintergreen Resort

4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

You're sure to have a blast at this incredible mountain condo! Condo is walking distance to the Wintergreen Resort Ski Lodge, Restaurants, The Market, and much more! This is the only condo neighborhood at Wintergreen that has it's own private outdoor pool. If you are up for a short drive down the mountain; check out the quality breweries, restaurants, distilleries, golf, and other fun activities near by! The Charlottesville area has been named 2023 Wine Region of the Year by Wine Enthusiast!

Guest favorite

Guesthouse in Gordonsville

4.91 out of 5 average rating, 182 reviews

La Petite Maison at Hedgeapple Hollow

La Petite Maison (our guest house) is the perfect place to simply get away from the hustle and bustle and relax! Sit in the private screen porch and watch the sun melt into the mountains. Deer, hummingbirds, bluebirds, and the occasional turkey like to hang out on the 8 acres of the property, perfect for any wildlife lover. Enjoy the fenced in common area featuring a seasonal in-ground pool. Conveniently situated near award-winning wineries, Montpelier, and historic downtown Gordonsville.

Top guest favorite

Home in McGaheysville

4.99 out of 5 average rating, 156 reviews

KinStay Massanutten Family Cabin - Room to Relax!

Great home in a prime location of the Massanutten Resort close to all the amenities: tubing, skiing/snowboarding, mini golf, GW Natl Forest, and Natl Park! Amazing outdoor activities all around! The home is tastefully furnished and well stocked for enjoying time with family and friends. Enjoy the gorgeous views from the spacious decks, relax in one of the two living rooms watching Netflix on the 65" TVs, or play a fun game of shuffleboard. So many ways to escape in this Massanutten home!

Superhost

Home in Wintergreen Resort

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

Guest favorite

Condo in Wintergreen Resort

4.94 out of 5 average rating, 226 reviews

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

Top guest favorite

Home in Robertson

4.93 out of 5 average rating, 216 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Superhost

Home in Town of Rockingham

4.78 out of 5 average rating, 260 reviews

Stone Spring - Heated Salt Pool - on 2.5 Acres

Heated Salt water pool and hot tub on 2.5 Acres. Lawn games & outdoor living room! New for '21 - Stove, Upstairs Flooring, Foosball Table, Board Games, paint New for '20 - Antimicrobial door handles, kitchen items Completely separate owner/caretakers quarters onsite, occupied by our property manager. Pool, hot-tub, grilling, etc are private spaces for guests and NOT shared *entrance and egress through pool area* *playhouse removed, gas fireplaces inoperable *no pets

Superhost

Home in Lovingston

4.85 out of 5 average rating, 297 reviews

Secluded Mountain Cabin w/ Pool, Trails & Winery ❤️

Nestled in Mountain Cove with views of Mountain Cove Winery, this property offers 100MB high-speed internet, adjacent to 800 acres of hiking trails. With an in-ground pool, deck, and firepit area, it's 35 minutes from Wintergreen, surrounded by wineries, breweries, and horseback riding. Ideal for creating memories. Note* Pool is not heated and closed when it’s cold. Ask before booking if the pool is open if you plan to swim.